| 2025 (1) Wynnewood over Sayre 34-14 |
| 2025 (Q) Pawhuska over Wynnewood 28-26 |
| 2024 (1) Fairview over Wynnewood 37-0 |
| 2022 (1) Wynnewood over Minco 26-20 |
| 2022 (2) Hooker over Wynnewood 41-32 |
| 2020 (1) Cashion over Wynnewood 56-6 |
| 2018 (1) Gore over Wynnewood 22-14 |
| 2017 (1) Ringling over Wynnewood 35-21 |
| 2016 (1) Wynnewood over Ringling 62-21 |
| 2016 (2) Wynnewood over Watonga 21-7 |
| 2016 (Q) Wynnewood over Crescent 35-18 |
| 2016 (S) Wynnewood over Morrison 20-14 |
| 2016 (C) Hominy over Wynnewood 42-14 |
| 2015 (1) Healdton over Wynnewood 32-15 |
| 2014 (1) Wynnewood over Rush Springs 33-0 |
| 2014 (2) Wynnewood over Hollis 26-20 |
| 2014 (Q) Wynnewood over Hominy 26-13 |
| 2014 (S) Thomas over Wynnewood 21-16 |
| 2013 (1) Wynnewood over Quinton 53-0 |
| 2013 (2) Kiefer over Wynnewood 20-12 |
| 2012 (1) Wynnewood over Gore 67-14 |
| 2012 (2) Wynnewood over Morrison 24-6 |
| 2012 (Q) Wynnewood over Thomas 42-21 |
| 2012 (S) Wynnewood over Cashion 41-28 |
| 2012 (C) Ringling over Wynnewood 39-12 |
| 2011 (1) Wynnewood over Wewoka 37-7 |
| 2011 (2) Woodland over Wynnewood 18-12 |
| 2010 (1) Wynnewood over Gore 46-10 |
| 2010 (2) Wynnewood over Foyil 34-14 |
| 2010 (Q) Thomas over Wynnewood 28-14 |
| 2009 (1) Talihina over Wynnewood 46-0 |
| 2007 (1) Rush Springs over Wynnewood 47-0 |
| 2005 (1) Wynnewood over Pocola 39-8 |
| 2005 (2) Pawnee over Wynnewood 21-0 |
| 2004 (1) Wynnewood over Keys (Parkhill) 21-14 |
| 2004 (2) Commerce over Wynnewood 48-20 |
| 2003 (1) Wynnewood over Quinton 56-6 |
| 2003 (2) Wynnewood over Woodland 17-7 |
| 2003 (Q) Ringling over Wynnewood 54-8 |
| 2002 (1) Wynnewood over Panama 23-7 |
| 2002 (2) Woodland over Wynnewood 27-6 |
| 2001 (1) Wynnewood over Henryetta 33-8 |
| 2001 (2) Millwood over Wynnewood 47-8 |
| 2000 (1) Holdenville over Wynnewood 42-0 |
| 1998 (1) Wynnewood over Marietta 42-35 |
| 1998 (2) Wynnewood over Watonga 24-21 |
| 1998 (Q) Tishomingo over Wynnewood 39-15 |
| 1997 (1) Wynnewood over Prague 32-20 |
| 1997 (2) Fairview over Wynnewood 35-12 |
| 1995 (1) Wynnewood over Kingston 39-9 |
| 1995 (2) Wynnewood over Watonga 34-18 |
| 1995 (Q) Davis over Wynnewood 35-14 |
| 1994 (1) Davis over Wynnewood 20-6 |
| 1993 (1) Wynnewood over Chandler 35-15 |
| 1993 (2) Hobart over Wynnewood 20-10 |
| 1992 (1) Wynnewood over Okemah 42-14 |
| 1992 (2) Wynnewood over Blanchard 27-8 |
| 1992 (Q) Wynnewood over Wewoka 26-15 |
| 1992 (S) Wynnewood over Hominy 46-24 |
| 1992 (C) Wynnewood over Watonga 27-22 |
| 1991 (1) Wynnewood over Stroud 42-6 |
| 1991 (2) Wynnewood over Hollis 36-14 |
| 1991 (Q) Wynnewood over Konawa 41-23 |
| 1991 (S) Wynnewood over Hartshorne 35-6 |
| 1991 (C) Wynnewood over Hobart 27-0 |
| 1990 (1) Wynnewood over Konawa 31-0 |
| 1990 (2) Wynnewood over Deer Creek 49-21 |
| 1990 (Q) Wynnewood over Hobart 21-0 |
| 1990 (S) Cascia Hall over Wynnewood 31-28 |
| 1989 (1) Wynnewood over Dibble 45-21 |
| 1989 (2) Wynnewood over Deer Creek 39-16 |
| 1989 (Q) Wynnewood over Alva 35-7 |
| 1989 (S) Okemah over Wynnewood 14-13 |
| 1988 (1) Wynnewood over Hobart 20-7 |
| 1988 (2) Wynnewood over Stroud 42-19 |
| 1988 (Q) Wynnewood over Marietta 36-22 |
| 1988 (S) Wynnewood over Kingston 34-23 |
| 1988 (C) Wynnewood over Nowata 35-7 |
| 1987 (1) Wynnewood over Hartshorne 12-0 |
| 1987 (2) Wynnewood over Haskell 21-14 |
| 1987 (Q) Wynnewood over Kingston 12-0 |
| 1987 (S) Wynnewood over Davis 20-14 |
| 1987 (C) Wynnewood over Hobart 21-14 |
| 1986 (1) Hobart over Wynnewood 28-0 |
| 1983 (1) Wynnewood over Crooked Oak 37-0 |
| 1983 (2) Wynnewood over Valliant 28-0 |
| 1983 (Q) Wynnewood over Purcell 12-6 |
| 1983 (S) Wynnewood over Hobart 12-0 |
| 1983 (C) Morris over Wynnewood 33-13 |
| 1981 (1) Wynnewood over Purcell 15-14 |
| 1981 (2) Stroud over Wynnewood 14-0 |
| 1980 (1) Wynnewood over Blanchard 12-7 |
| 1980 (2) Holdenville over Wynnewood 34-16 |
| 1977 (1) Wynnewood over Healdton 12-7 |
| 1977 (2) Newcastle over Wynnewood 27-10 |
| 1974 (1) Millwood over Wynnewood 20-7 |
| 1973 (1) Wynnewood over Hobart 34-0 |
| 1973 (Q) Wynnewood over Healdton 31-0 |
| 1973 (S) Wynnewood over Millwood 14-14 |
| 1973 (C) Hominy over Wynnewood 21-0 |
| 1967 (1) Velma-Alma over Wynnewood 34-6 |
| 1965 (1) Wynnewood over Walters 40-12 |
| 1965 (Q) Wynnewood over Bethany 20-0 |
| 1965 (S) Wynnewood over Carnegie 22-0 |
| 1965 (C) Wynnewood over Stigler 8-0 |
| 1961 (1) Wynnewood over Ringling 14-6 |
| 1961 (Q) Lawton Douglass over Wynnewood 12-12 |
| 1949 (1) Wynnewood over Moore 23-0 |
| 1949 (Q) Wynnewood over Waurika 25-7 |
| 1949 (S) Wynnewood over Alva 20-14 |
| 1949 (C) Wynnewood over Checotah 7-0 |
| 1948 (1) Wynnewood over Crooked Oak 13-13 |
| 1948 (Q) Waurika over Wynnewood 21-13 |